Methanesulfonyl chloride → 3-(4-Phenylthiazol-2-yl)propyl methanesulfonate

HRID 1397334Notes

Reaction equation

HRID 1397334 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([CH2:12][CH2:13][CH2:14][OH:15])[S:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>N1C=CC=CC=1>[CH3:16][S:17]([O:15][CH2:14][CH2:13][CH2:12][C:9]1[S:10][CH:11]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]=1)(=[O:19])=[O:18]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 673252893-(4-Phenylthiazol-2-yl)propan-1-ol

Product 1

HCID 866775933-(4-Phenylthiazol-2-yl)propyl methanesulfonateYield 74%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 3-(4-phenylthiazol-2-yl)propan-1-ol (0.4 g, 1.82 mmol) in dry pyridine (8 mL) was cooled to 0° C. and methanesulfonyl chloride (0.43 mL, 5.47 mmol) was added dropwise. The reaction mixture was allowed to warm up to room temperature, stirred for 1 h, and quenched with ice water. The organic product was extracted with EtOAc and organic layer was washed with brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure to afford 3-(4-phenylthiazol-2-yl)propyl methanesulfonate (0.4 g, yield 74%) as a pale yellow liquid, which was carried through without further purification. 1H NMR (300 MHz, CDCl3) δ 7.90-7.87 (m, 2H), 7.46-7.40 (m, 2H), 7.37-7.31 (m, 2H), 4.42-4.38 (t, J=6.1 Hz, 2H), 3.24-3.19 (t, J=7.2 Hz, 2H), 3.04 (s, 3H), 2.39-2.30 (m, 2H). MS (ESI) m/z: Calculated for C13H15NO3S2: 297.05. found: 298.0 (M+H)+.

Workup

  1. customquenched with ice water
  2. extractionThe organic product was extracted with EtOAc and organic layer
  3. washwas washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b2a893e602294632b462862e398ed08e
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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